(2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate

Base Information

• Chemical Name: (2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate
• CAS No.: 142980-91-4
• Molecular Formula: C₁₇H₃₂O₃Si
• Molecular Weight: 312.525
• Mol file: 142980-91-4.mol

Synonyms:(2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate

Chemical Property of (2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate

There total 9 articles about (2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

tert-butyldimethylsilyl chloride (18162-48-6) + [(2S,5S)-5-Hydroxy-2-methyl-cyclohex-(E)-ylidene]-acetic acid ethyl ester (145260-95-3) → (2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate (142980-91-4)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85618-0

Reference yield: 93.0%

ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate (142980-90-3) → (2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate (142980-91-4)

Guidance literature:

With Martins sulfurane; In tetrachloromethane; for 70h; Ambient temperature;

DOI:10.1021/jo00045a038

Reference yield:

(-)-dihydrocarvone (5524-05-0,619-02-3) → (2E)-ethyl <(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanoate (142980-91-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 1) NaH / 1) THF, a) -20 deg C, 1 h, b) r.t., 2 h, 2) r.t., 24 h

3: 95 percent / imidazole / dimethylformamide

With 1H-imidazole; sodium hydride; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)85618-0

upstream raw materials:

tert-butyldimethylsilyl chloride

[(2S,5S)-5-Hydroxy-2-methyl-cyclohex-(E)-ylidene]-acetic acid ethyl ester

ethyl <(1'R,2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-1'-hydroxy-2'-methylcyclohexyl>ethanoate

(S)-p-mentha-6,8-dien-2-one

Downstream raw materials:

(2E)-2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethanol

(2E)-<2-<(2'S,5'S)-5'-<(tert-butyldimethylsilyl)oxy>-2'-methylcyclohexylidene>ethyl>diphenylphosphine oxide

25-hydroxydihydrotachysterol₂

Dihydrotachysterol₂